Fragrance composition containing 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives

ABSTRACT

4-(1-methoxymethyl)-2-phenyl-1,3-dioxolane or a derivative thereof represented by formula (I): ##STR1## wherein R 1  represents a hydrogen atom, a hydroxy group or a lower alkoxy group; R 2  and R 3 , which may be the same or different, each represents a hydrogen atom, a hydroxy group, a lower alkoxy group, or, when taken together, R 2  and R 3  represent a methylene dioxy group; useful in flavor and fragrance compositions.

This application is a continuation-in-part application of and claims priority for U.S. Ser. No. 08/321,976, filed Oct. 12, 1994, now U.S. Pat. No. 5,545,424.

FIELD OF THE INVENTION

This invention relates to 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives which are useful as an active ingredient for flavor or fragrance compositions.

BACKGROUND OF THE INVENTION

Various types of products incorporate ingredients which impart some kind of sensation to the mouth, oral cavity, throat or skin as a flavor or fragrance. Such products include toothpastes, mouthwashes, chewing gums, tobacco products, beverages and pharmaceutical products.

For example, 1-menthol and 3-(1-menthoxy)propane-1,2-diol are used as active ingredients in the products described above (e.g., as disclosed in U.S. Pat. No. 4,459,425). These products impart a cooling sensation to the mouth or skin.

PCT published application WO 92/10107 discloses that compound (II) represented by the following general formula: ##STR2## wherein R⁴ and R⁵ are independently --COOR⁶ wherein R⁶ is H or lower alkyl, provided that in at least one of R⁴ and R⁵, R⁶ is lower alkyl; wherein Z is a direct bond, or --CH═C(R⁷)--; where R⁷ is H or an alkyl group; and Y is a group of the formula (III) or (IV): ##STR3## where R⁸ and R⁹ are independently H, lower alkyl or --OR¹⁰ where R¹⁰ is H or lower alkyl; is useful as a flavor.

However, an ingredient which can impart a more significant and/or stimulating sensation is desired for the consumer market. Moreover, such an ingredient must have good quality and have a long-lasting taste, odor or combination thereof.

On the other hand, it has been disclosed that a substituted benzaldehyde acetal compound represented by general formula (V): ##STR4## wherein R¹¹ is C₁₋₂ alkyl, R¹² and R¹³ are each lower alkyl or R¹² and R¹³, together with oxygen atom to which they bond may form, a cyclic group of the formula --O--R¹⁴ --O-- where R¹⁴ is a lower alkylene or alkylalkylene which may be substituted with a lower alkyl or OH;

is useful as a flavor and a fragrance (as disclosed in JP-A-57-188537 and WO 94/06441) (The term "JP-A" as used herein means an "unexamined published Japanese patent application").

However, those compounds do not impart a stimulating sensation or a long-lasting sensation to the mouth or skin.

SUMMARY OF THE INVENTION

Accordingly, an object of this invention is to provide a new flavor and fragrance compound while meeting the above-described requirements.

In view of the above, extensive investigations have been conducted and, as a result, this invention provides 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives with enhanced taste and odor and thus a long-lasting taste and odor is achieved.

The present invention provides 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or a derivative thereof represented by formula (I): ##STR5## wherein R¹ represents a hydrogen atom, a hydroxy group or a lower alkoxy group, R² and R³, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a lower alkoxy group, or when taken together, R² and R³ represent a methylene dioxy group.

The present invention further provides a flavor or fragrance composition containing the compound of formula (I) or a derivative thereof as an active ingredient.

DETAILED DESCRIPTION OF THE INVENTION

In formula (I), the lower alkoxy group as represented by R¹, R² and R³ preferably contains from 1 to 4 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butyloxy group and an isobutyloxy group.

More preferably, specific examples include a methoxy group and an ethoxy group.

Furthermore, specific examples of the preferred compound of the present invention represented by the formula (I), are compounds shown in Table 1 below, but the compounds of the formula (I) are not limited to these exemplified compounds.

In addition, in Table 1, Me, Et, Pr, and n-Bu represents a methyl group, an ethyl group, a propyl group, and an n-butyl group respectively.

                  TABLE 1                                                          ______________________________________                                         Compound R.sup.1                                                                               R.sup.2   R.sup.3                                                                              Name                                           ______________________________________                                         1        H      H         H     4-(1-menthoxy-methyl)-                                                         2-phenyl-1,3-dioxolane-                                                        (Genzaldehyde-MPD)                             2        H      OH        OH    4-(1-menthoxy-methyl)-                                                         2-(3',4'-                                                                      dihydroxyphenyl)-1,3-                                                          dioxolane                                                                      (protocatechuic                                                                aldehyde-MPD)                                  3        H      OME       OH    4-(1-menthoxy-methyl) -                                                        2-(3'-methoxy-4'-                                                              hydroxyphenyl)-1,3-                                                            dioxolane(vanillin-                                                            MPD)                                           4        H      OEt       OH    4-(1-menthoxy-                                                                 methyl)-2-(3'-ethoxy-                                                          4'-hydroxyphenyl)-1,3-                                                         dioxolane(ethyl                                                                vanillin-MPD)                                  5        OH     OMe       H     4-(1-menthoxy-methyl)-                                                         2-(2'-hydroxy-3'-                                                              methoxy-phenyl)-1,3-                                                           dioxolane(ortho                                                                vanillin-MPD)                                  6        H      H         OMe   4-(1-menthoxy-methyl)-                                                         2-(4'-methoxyphenyl)-                                                          1,3-dioxolane                                                                  (anisaldehyde-MPD)                             7        H      --O--CH.sub.2                                                                            --O-- 4-(1-menthoxy-methyl)-                                                         2-(3',4'-methylenedio                                                          xyphenyl)-1,3-                                                                 dioxolane(piperonal-                                                           MPD)                                           ______________________________________                                    

The abbreviations in Table 1 above are described below:

MPD represents an acetal of 3-(1-menthoxy)propanediol.

Of these compounds, preferred examples include Compound 2 and Compound 3.

4-(1-Menthoxymethyl)-2-phenyl-1,3-dioxolane or derivatives of formula (I) can be produced, for example, using the following Reaction Scheme. ##STR6##

That is, 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives of formula (I) can be easily synthesized by reaction of 3-(1-menthoxypropane-1,2-diol (2) with a benzaldehyde derivative (3) in the presence of an acid as a catalyst.

Examples of suitable benzaldehyde derivatives (3) include vanillin, protocatechuic aldehyde, ethyl-vanillin, ortho-vanillin, benzaldehyde, anisaldehyde and piperonal (heliotropin).

Suitable acids useful as a catalyst include any acid which is typically used in acetalization. Examples of suitable acids include hydrochloric acid, phosphoric acid, sulfuric acid, p-toluene sulfonic acid, acetic acid, anhydrous acetic acid, and propionic acid.

The reaction can be conducted in a similar manner to conventional acetalization chemistry.

It was found that the 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives (I) obtained enhance taste or odor with a long-lasting taste and odor being produced.

Furthermore, it surprisingly turned out that the taste given off by the thus obtained 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives (I) provides new and unexpected flavor characteristics.

For example, 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane (Compound 3, vanillin-MPD) of the present invention has a hot, burning and tingling taste with a long-lasting taste.

Compound 3 is derived from vanillin and 3-(1-menthoxy)-1,2-propanediol. Vanillin is a common flavor or fragrance ingredient which is very sweet and has a strong vanilla-like odor. 3-(1-Menthoxy)-1,2-propanediol (produced by TAKASAGO INTERNATIONAL CORPORATION, U.S. Pat. No. 4,459,425) is also a flavor or fragrance ingredient which has a menthol-like taste and a cooling effect.

That is, the character of Compound 3 of the present invention is different from that of those prior art compounds described above.

Compound (I) of the present invention can be used to prolong other sensations such as cooling sensations, for example, in combination with 1-menthol, 3-(1-menthoxy)-1,2-propanediol or isopulegol. When cooling and longer lasting tingling sensations are added together, the result would signal prolonged cooling effects to the user.

The burning tingling or bitter sensations are desirable as signals to convey to the user a desired psychological or physiological effect.

Compound (I) of the present invention can be used in confectionery, beverages and other foods. More specifically, it can be used in chewing gums, candies, ice creams, ice candies, chocolates, snacks, cookies, cakes, breads, tea, coffee, juice, fruit wine, dairy drinks, carbonated drinks, etc.

Also, Compound (I) of the present invention can be used in cosmetic and pharmaceutical products. More specifically, it can be used in mouthwashes, toothpastes, antiperspirant products, deodorant products, colognes, perfumes, lip sticks, soaps, shampoos, hair rinses and detergents, etc.

A suitable amount of 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives (I) according to the present invention which is used in a flavor composition or in a fragrance composition to be used in various products, wherein the amount used is from 0.0001 to 30% by weight, preferably from 0.0001 to 10% by weight and more preferably from 0.001 to 0.01% by weight, based on the total weight of the composition.

Although many novel synthesized molecules have various effects on the skin, they are often toxic and cannot be applied every day. In contrast, the present invention produces novel compounds that are safe for human skin.

The two main moieties, 3-1-menthoxy propane-1,2-diol and an aromatic aldehyde, of the present invention are widely used as flavor and fragrance components. The present compounds are readily hydrolyzed in the stomach, at approximately pH 2 and are therefore, safe for use.

The present invention is now illustrated in greater detail with reference to the following synthesis examples, examples and comparative examples. However, these synthesis examples, examples and comparative examples are not to be construed to limit the scope of the invention.

The analytical instruments used in the synthesis examples of the present specification were as follows:

(1) Nuclear magnetic resonance spectrum (¹ H-NMR):GSX-500 (500 MHz) (manufactured by JEOL)

(2) Mass spectrum (MS):JMS-DX303HF (manufactured by JEOL).

Unless otherwise indicated herein, all parts, percentages, ratios and the like are by weight.

SYNTHESIS EXAMPLE 1 Synthesis of Vanillin-MPD

To a 1.0 liter 2-neck round bottom flask, under a dry nitrogen atmosphere, was added 3,-1-menthoxypropane-1,2-diol (MPD)(17.0 g, 73.9 mmoles), followed by sequential addition of dry toluene (500 ml), vanillin (11.25 g, 73.9 mmoles) and p-toluene sulfonic acid monohydrate (141 mg, 0.74 mmoles).

The flask was equipped with a Dean-Stark apparatus filled with 3A molecular sieves. The mixture was refluxed under a dry nitrogen atmosphere for 42 hours at which time the reaction was determined to be complete by chromatographic analysis.

After cooling to room temperature (about 20° C.-30° C.), the solvent was removed under reduced pressure to obtain a crude oily residue. Purification of the crude oily residue by flash chromatography (silica gel Si-60, ethyl acetate/hexane=1/5 (by volume)) gave pure vanillin-MPD (17.8 g, 48.9 mmoles, 59.4% of theoretical yield).

¹ H-NMR (500 Mhz, CDCl₃, δ ppm): 0.76-0.09 (m, 11 H), 1.25 (m, 1H), 1.35 (m, 1H), 1.62 (m, hZ), 2.1 (m, 1H), 2.2 (m, 1H, 3.1 (m, 1H), 3.3 (m, 1/2H), 3.4 (m, 1/2H), 3.54 (m, 1H), 3.66 (m, 1/2H), 3.75 (m, 1/2H), 3.85 (m, 1/2H), 3.91 (s, 3H), 3.96 (m, 1/2H), 4.08 (m, 1/2H), 4.25 (m, 1/2H), 4.35 (m, 1H), 5.66 (s, 1H), 5.73 (s, 1/2H), 5.8 (s, 1/2H), 6.91 (m, 1H), 6.99 (m, 2H) MS (m/z): 364 (M+).

SYNTHESIS EXAMPLES 2 to 7

4-(1-Menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives as shown in Table 2 below were prepared in the same manner as in Synthesis Example 1 above, except for replacing the substrate, vanillin, with each of the benzaldehyde or its derivatives as shown in Table 2 below.

                  TABLE 2                                                          ______________________________________                                                               4-(1-Menthoxy-                                           Synthesis             methyl)-2-phenyl-                                                                           Isolated                                    Example               1,3-dioxolane or its                                                                        Yield                                       No.       Substrate   Derivative Produced                                                                         (%)                                         ______________________________________                                         2         Protocatechuic                                                                             Protocatechuic                                                                              22.0                                                  aldehyde    aldehyde-MPD                                             3         Ethyl vanillin                                                                             Ethyl vanillin-MPD                                                                          22.0                                        4         Ortho vanillin                                                                             Ortho vanillin-MPD                                                                          44.0                                        5         Benzaldehyde                                                                               Benzaldehyde-MPD                                                                            63.2                                        6         Anisaldehyde                                                                               Anisaldehyde-MPD                                                                            33.5                                        7         Piperonal   Piperonal-MPD                                                                               52.2                                        ______________________________________                                    

Spectral data for each is shown below.

Protocatechuic aldehyde-MPD

¹ H-NMR (500 Mhz, CDCl₃, δ ppm): 5.64 (s, 1/2H, acetal), 5.80 (s, 1/2H, acetal), 6.55 (br s, 2H, --OH) MS (m/z): 350 (M⁺)

Ethyl vanillin-MPD

¹ H-NMR (500 Mhz, CDCl₃, δ ppm): 1.44 (t, 3H, --CH₃), 4.14 (q, 2H, --OCH₂ --), 5.72 (s, 1/2H, acetal), 5.72 (s, 1H, --OH), 5.83 (s, 1/2H, acetal) MS (m/z): 378 (M⁺)

Ortho-vanillin-MPD

¹ H-NMR (500 Mhz, CDCl₃, δ ppm): 3.82 (s, 3H, --OCH₃), MS (m/z): 364 (M⁺)

Benzaldehyde-MPD

¹ H-NMR (500 Mhz, CDCl₃, δ ppm): 5.80 (s, 1/2H, acetal), 5.93 (s, 1/2H, acetal) MS (m/z): 318 (M⁺)

Anisaldehyde-MPD

¹ H-NMR (500 Mhz, CDCl₃, δ ppm): 3.82 (s, 3H, --OHC₃), 5.76 (s, 1/2H, acetal), 5.88 (s, 1/2H, acetal) MS (m/z): 348 (M⁺)

Piperonal-MPD

¹ H-NMR (500 Mhz, CDCl₃, δ ppm) 5.71 (s, 1/2H, acetal), 5.96 (s, 1/2H, acetal), 5.96 (s, 2H, acetal) MS (m/z): 362 (M⁺)

Example 1 Mouth Sensation of Compounds

Odor evaluation and mouth sensation evaluation were carried out on each compound synthesized in the foregoing Synthesis Examples. The results obtained are shown in Table 3 below.

                  TABLE 3                                                          ______________________________________                                                                      Longevity                                                                             Longevity*                                          Characteristic                                                                            Mouth    of Mouth                                                                              of odor on                                 Compound Odor       Sensation                                                                               Sensation                                                                             blotting paper                             ______________________________________                                         Vanillin-MPD                                                                            dilute     hot,     3-4 hours                                                                             >30 days                                            vanilla/odor                                                                              tingling,                                                                      burning,                                                                       numbing                                                    Protocatechuic                                                                          medicinal  hot,     3-4 hours                                                                             --                                         aldehyde-MPD        pepper,                                                                        burning                                                    Ethyl    vanilla, sweet                                                                            oily,    --     >30 days                                   vanillin-MPD        metallic                                                   Ortho    medicinal, bitter,  --     --                                         vanillin-MPD                                                                            vanilla    slightly                                                                       hot                                                        Benzaldehyde-                                                                           sweet, floral                                                                             bitter   --     >30 days                                   MPD                                                                            Anisaldehyde-                                                                           anisyl odor,                                                                              slight   10-15  >30 days                                   MPD      sweet      sweet,   minutes                                                               slippery,                                                                      creamy                                                     Piperonal-MPD                                                                           floral, sweet                                                                             bitter   10     >30 days                                                                minutes                                           ______________________________________                                          *Each compound is soaked into a blotting paper and the longevity of the        odor is evaluated.                                                       

Example 2 Mouth Sensation Enhancement

Compounds of the present invention were tasted pure in small amounts on a wooden toothpick. Thermally hot tea was ingested after a short time.

The temperature of tea was determined subjectively by sipping a cup of tea. In the test, a small amount of vanillin-MPD was applied to the mouth via a wooden toothpick before sipping the tea. In the control, no addition treatment was used.

The compound of the present invention enhanced the thermally hot sensation to cause the tea to taste hotter in comparison with the tea consumed without the compound of this invention.

The results obtained are shown in Table 4 below.

                  TABLE 4                                                          ______________________________________                                                    Heat Determination                                                               Within 3 min.                                                                             After 30 min.                                          ______________________________________                                         Control        hot          warm                                               Test Compound  very hot     hot                                                ______________________________________                                    

Example 3

A 1000 ppm ethanol solution of vanillin-MPD was prepared. Using this stock solution, a series of 5 ml samples of vanillin-MPD diluted with water were prepared at 100 ppm, 10 ppm and 1 ppm concentrations.

The procedure used for tasting the samples was as follows. The most dilute sample was tasted first. The sample was gargled for 30 seconds followed by spitting out the solution. Comments were recorded and the next sample was tasted when no effect of the previous sample remained in the mouth.

The results obtained are shown in Table 5 below.

                  TABLE 5                                                          ______________________________________                                         Vanillin-                                                                              Time                                                                   MPD     2-3 min.  10-15 min. 30 min. 120 min.                                  ______________________________________                                         1 ppm   bitter on                                                                      sides of                                                                       tongue,                                                                        slight                                                                         tingling,                                                                      numbing on                                                                     lips                                                                   10 ppm  very                                                                           bitter, hot                                                                    sensation                                                                      on roof of                                                                     mouth and                                                                      throat                                                                 100 ppm very hot  low level  low level                                                                              low level                                         taste,    hot, sinus hot, sinus                                                                             hot, sinus                                        bitter    clearing   clearing                                                                               clearing                                          taste     effect,    effect, effect,                                                     numbing    numbing numbing                                   ______________________________________                                    

Comparative Example 1

Each compound was tasted in the same manner as in Example 3.

The results obtained are shown in Table 6 below. In the table, vanillin-PGA represents propylene glycol acetal of vanillin and vanillin-DEA represents diethyl acetal of vanillin.

                  TABLE 6                                                          ______________________________________                                         Compound  Concentration                                                                              Characteristics                                          ______________________________________                                         Vanillin-MPD                                                                             neat        hot, bitter, numbing, lasts over                                               4 hours                                                  Vanillin-PGA                                                                             neat        hot bitter taste, lasts only 2-3                                               minutes                                                  Vanillin-DEA                                                                             neat        hot bitter taste, lasts only 2-3                                               minutes                                                  Vanillin-DEA                                                                             100 ppm     momentary warm, bitter,                                                        sensation is gone in 30 seconds.                         ______________________________________                                    

Vanillin-MPD, vanillin-PGA and vanillin-DEA produce hot sensations at slightly different sites in the mouth. Vanillin-MPD is hotter than vanillin-PGA or -DEA.

Example 4 Hard Candy

A hard candy was prepared using 0.0001 to 10% by weight (1 to 100 ppm) of vanillin-MPD as follows:

1 cup of light corn syrup

1 cup of water

2 cups of sugar

1/4 teaspoon of flavoring

1/4 teaspoon of food coloring

0.0001 or 0.1% by weight of vanillin-MPD

The corn syrup, water and sugar were combined in a 2-quart saucepan. The mixture was heated to 300° F. (150° C.) and then removed from the heat. The flavoring, food coloring and vanillin-MPD were then added to the mixture, stirred until blended, poured free-form or into molds and cooled to room temperature to produce a hard candy.

The hard candy thus obtained was tasted and evaluated. The results obtained are shown in Table 7 below.

                  TABLE 7                                                          ______________________________________                                         Vanillin-                                                                              Time                                                                   MPD     2-3 min.  10-15 min. 30 min.  90 min.                                  ______________________________________                                         1 ppm   slight hot                                                                               slight hot                                                           taste,    taste,                                                               prickly,  prickly,                                                             numbing   numbing                                                      100 ppm hot taste,                                                                               hot taste, hot taste,                                                                              hot                                              prickly,  prickly,   prickly, taste,                                           numbing   numbing,   numbing, prickly,                                                   warming    warming  numbing                                                    sensation  sensation                                                           spread down                                                                               spread down                                                         to throat  to throat                                         ______________________________________                                    

At 100 ppm, vanillin-MPD has a hot taste with a prickly, numbing effect that is mainly on the tongue. It lasts on the tongue for over 90 minutes. This effect spreads throughout the oral cavity. As a result, there is a warming sensation that spreads to the back of the mouth and down the throat. This warming sensation does not last as long as the hot taste, prickly, numbing effects on the tongue.

While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.

Example 5 Fragrance Composition

A fragrance composition (A) or (B) having the following formulation is prepared.

    ______________________________________                                         Formulation         Parts Per 100                                              ______________________________________                                         Formulation of fragance composition (A):                                       Gardenia oil        45                                                         Vanillin-MPD        15                                                         rosewood oil        15                                                         rose oil            25                                                         Formulation of fragrance composition (B)                                       Dodecahydro-3a,6,6,9a-tetramethyl-                                                                 10                                                         naphtho 2,1-b!furan                                                            Armoise oil         1                                                          Basil oil           1                                                          Ciste labdanum sis abs                                                                             1                                                          Citronellol         5                                                          Cresyl acetate      0.5                                                        2,6,6-trimethyl-trans-1-crotonyl-                                                                  5                                                          cyclohexene-1                                                                  Eugenol             1                                                          Galbanum oil 10%    1                                                          Methyl dihydrojasmonate                                                                            25                                                         2-acetyl-1,2,3,4,6,7,8-octahydro-                                                                  20                                                         2,3,8,8-tetramethylnaphthalene                                                 Lemon oil           5                                                          10-oxahexadecanolide                                                                               7                                                          Methyl-2,2,3-cyclopenten-3-yl-1)-5-                                                                10                                                         pentanol-2                                                                     p-isobutyl-α-methyl-                                                                         5                                                          dihydrocinnamaldehyde                                                          Vanillin-MPD        5                                                          Ylang oil extra     1                                                          ______________________________________                                    

Vanillin-MPD is preferably formulated into a fragrance composition in an amount of from 0.1% to 30% by weight based on the total weight of the composition.

The fragrance composition comprising 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or a derivative thereof according to the present invention, can further be incorporated into a product, such as a product containing alcohol, preferably in an amount of from 10% to 30% by weight, or in an air freshener product in the form of a solid, a powder, an incense, a gel, a cream, a spray or a liquid, preferably in an amount of from 25% to 55% by weight based on the total weight of the product.

Example 6 Cream

A cream having the following formulation is prepared.

    ______________________________________                                         Cream formulation      Parts                                                   ______________________________________                                         Polypropylene stearyl ether (arlamol E)                                                               20                                                      Vanillin-MPD           5.0                                                     Stearyl alcohol        4.0                                                     Steareth 2 (brij 72)   3.4                                                     Steareth 21 (brij 721) 1.64                                                    Methyl paraben         0.02                                                    Water                  65.84                                                   ______________________________________                                    

Vanillin-MPD is preferably formulated into a cosmetic product, such as a cream, in an amount of from 0.005% to 5% by weight, based on the total weight of the product.

Comparative Example 2 Cream

A cream is prepared in the same manner as in Example 6, except that Vanillin is used in place of Vanillin-MPD.

EVALUATION EXAMPLE 1 Stability of Cream

    ______________________________________                                                 Color         Odor                                                     Cream     Initial After 1 week                                                                               Initial                                                                              After 1 week                               ______________________________________                                         vanillin  White   Tan, off white                                                                             vanilla                                                                              sour note                                  (Comp. Ex. 2)                 note                                             vanillin-MPD                                                                             White   White       vanilla                                                                              vanilla                                    (Ex. 6)                       note  note                                       ______________________________________                                    

The enhanced stability of vanillin-MPD to discoloration is illustrated by the above example. Vanillin and vanillin-MPD were added to a standard lotion cream base (both at 5%). After one week at room temperature, the vanillin lotion had discolored to an off-white tan color, while the vanillin-MPD lotion remained unchanged.

EVALUATION EXAMPLE 2 Odor of Cream

    ______________________________________                                         Cream          After 1.5 hour                                                                               After 3 hours                                     ______________________________________                                         vanillin       vanilla odor  no odor                                           (Comp. Ex. 2)                                                                  vanillin-MPD   vanilla odor  vanilla odor                                      (Ex. 6)                                                                        ______________________________________                                    

Each cream was respectively applied to the back of the hand. The vanillin cream had an immediate off vanilla odor that lasted 1.5 hours. The vanillin-MPD cream had a slight initial vanilla odor, which increased and lasted for 3 hours. 

What is claimed is:
 1. A fragrance composition comprising a fragrance effective amount of 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or a compound represented by formula (I): ##STR7## wherein R¹ represents a hydrogen atom, a hydroxy group or a lower alkoxy group; R² and R³, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a lower alkoxy group, or, when taken together, R² and R³ represents a methylene dioxy group and an acceptable carrier.
 2. A fragrance composition comprising 4-(1-menthoxymethyl)-2-phenyl)-1,3-dioxolane or a compound thereof represented by formula (I) as in claim 1, wherein R¹ is a hydrogen atom, R² is a methoxy group and R³ is a hydroxy group.
 3. A fragrance composition comprising 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or a compound thereof represented by formula (I) as in claim 1, wherein R¹ is a hydrogen atom, R² is a hydroxy group and R³ is a hydroxy group.
 4. A fragrance composition as in claim 1, wherein said 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or a compound thereof represented by formula (I) is present in an amount of from 0.0001 to 30% by weight based on the total weight of the composition.
 5. A fragrance composition comprising 4-(1-menthoxymethyl)-2-phenyl)-1,3-dioxolane or a compound thereof represented by formula (I) as in claim 1, whereinR¹ is a hydrogen atom, R² is an ethoxy group and R³ is a hydroxy group.
 6. A fragrance composition comprising 4-(1-menthoxymethyl)-2-phenyl)-1,3-dioxolane or a compound thereof represented by formula (I) as in claim 1, whereinR¹ is a methoxy group, R² is a hydroxy group and R³ is a hydrogen atom.
 7. A fragrance composition comprising 4-(1-menthoxymethyl)-2-phenyl)-1,3-dioxolane or a compound thereof represented by formula (I) as in claim 1, whereinR¹ is a hydrogen atom, R² is a hydrogen atom and R³ is a methoxy group. 